The present invention relates to methods for producing (Z)-2-benzoyloxy-12-heptadecene and optically active (2S,12Z)-2-hydroxy-12-heptadecene, and a method for producing optically active (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a pheromone component of pistachio twig borer that is a major insect pest of pistachio trees.
Pistachio twig borer (scientific name: Karmania pistaciella) is a significant insect pest of pistachio trees in Iran, Turkey and the like. Larvae of the insect damage pistachio trunks and cause serious problems such as reductions in crop yield and crop quality. At the present time, insecticides are used to control the pistachio twig borer but achieve an insufficient effect and may cause environmental and human health concerns. In such circumstances, there is a demand for the development of novel insect pest control techniques such as mating disruption and mass trapping by using a sex pheromone of the insect.
As a sex pheromone of the pistachio twig borer, R. Gries et al. reported optically active (2S,12Z)-2-acetoxy-12-heptadecene in 2006 (see WO 2007/079563 (Turkish Patent Application Publication No. 200805195) and R. Gries et al., J. Chem. Ecol., (2006) 32:2667). It is also found that (2R,12Z)-2-acetoxy-12-heptadecene, the stereoisomer of the above compound, exhibits an attraction-inhibiting effect (see WO 2007/079563 (Turkish Patent Application Publication No. 200805195) and R. Gries et al., J. Chem. Ecol., (2006) 32:2667).
R. Gries et al. also disclose methods for producing (2S,12Z)-2-acetoxy-12-heptadecene, the sex pheromone of the pistachio twig borer. In one method, optical resolution is used in which racemic (2RS,12Z)-2-hydroxy-12-heptadecene is reacted with vinyl acetate in the presence of a lipase as an esterase to obtain (2S,12Z)-2-hydroxy-12-heptadecene, and the obtained (2S,12Z)-2-hydroxy-12-heptadecene is acetylated; and in the other method, optically active (S)-propylene oxide is used (see WO 2007/079563 (Turkish Patent Application Publication No. 200805195) and R. Gries et al., J. Chem. Ecol., (2006) 32:2667).